Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Inherently Chiral Calix[4]arene

  • Published : 1995.11.20
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Abstract

Three inherently chiral calix[4]arenes 3-5 were synthesized as racemate starting from the ethylation at 1.3-distal hydroxy groups of calix[4]arene 2 which has two phenyl groups at upper rim in AABB fashion, and then two remaining hydroxy groups were acetylated by treatment with acetyl chloride in the presence of NaH to produce calix[4]arene 4. Treatment of 4 with AlCl3 under Fries rearrangement conditions, only one acetyl group was rearranged to the para-position to afford calix[4]arene 5 with AABC substitution pattern at the upper rim of calix. The structure of chiral calix[4]arenes were confirmed based on NMR and massspectra.

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